Take 20 on Search for a 24 total on the Search Check.
Jessie Tosscobble III's AppearanceJessie is small standing at 2 foot 8 inches and weighing a mere 27 pounds. As such, the lass intentionally keeps her brown hair long to cover her halfling features, which allows the rogue to pass herself off as a small humanoid or even young human or half-elven child when convenient or necessary.
Dressed dark purple clothing, which is overlaid with attractive black leather accoutrements, Jessie keeps the paraphernalia of her 'profession' secreted upon her person, and especially the authorities, except when in use.
Her friendly blue eyes and warm, sincere smile are disarming and allow the lass to paint a picture of a young girl who is completely unintimidating by all appearances, an assumption often made by others which suits her well and which she actively cultivates.
To promote this look of youth or innocence, most of Jessie's weapons, alchemical doodads, pack, and other equipment are kept hidden under her clothing and also by her large heavy dark green cloak.